Triethylamine → 6,7-Dimethyl-4,9-bis[(trimethylsilyl)ethynyl][1,2,5]thiadiazolo[3,4-g]quinoxaline

HRID 1176158Notes

Reaction equation

Br[C:2]1[C:3]2[C:4](=[N:15][S:16][N:17]=2)[C:5](Br)=[C:6]2[C:11]=1[N:10]=[C:9]([CH3:12])[C:8]([CH3:13])=[N:7]2.C1C=CC([As](C2C=CC=[CH:35][CH:36]=2)C2C=CC=CC=2)=CC=1.[CH3:37][Si:38]([C:41]#[CH:42])([CH3:40])[CH3:39].CCN(CC)CC>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1COCC1>[CH3:12][C:9]1[C:8]([CH3:13])=[N:7][C:6]2[C:11](=[C:2]([C:35]#[C:36][Si:38]([CH3:40])([CH3:39])[CH3:37])[C:3]3[C:4](=[N:15][S:16][N:17]=3)[C:5]=2[C:42]#[C:41][Si:38]([CH3:40])([CH3:39])[CH3:37])[N:10]=1

Participants

Conditions

Temperature: 45 °C

Procedure

4,9-Dibromo-6,7-dimethyl[1,2,5]thiadiazolo[3,4-g]quinoxaline (68.0 mg, 1.82×10−4 mol), Pd2dba3 (36.0 mg, 3.93×10−5 mol), AsPh3 (62.2 mg, 2.03×10−4 mol), (trimethylsilyl)acetylene (0.60 ml, 4.2×10−3 mol), Et3N (2.0 ml), and THF (15 ml) were added to a 100-ml Schlenk tube. The reaction mixture was stirred at 45° C. for 18.5 h under N2. After the solvent was evaporated, the residue was chromatographed on silica gel using 8:1 hexanes:THF as the eluant. Yield=0.051 g (69% based on 68.0 mg of 4,9-dibromo-6,7-dimethyl[1,2,5]thiadiazolo[3,4-g]quinoxaline). 1H NMR (360 MHz, CDCl3): δ 2.83 (s, 6H, —CH3), 0.42 (s, 18H, —Si—CH3). Chemical Ionization MS m/z: 408.1264 (M+) (calcd 408.126).

Workup

customAfter the solvent was evaporated
customthe residue was chromatographed on silica gel using 8:1 hexanes

Sources & evidence

ORD record: ord-f19d366aaeb6435394e8013117fc5e16
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07842758B2

Reaction notes

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